1,3-Dimethyl-2-isopropyl-benzol | 14411-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-Dimethyl-2-isopropyl-benzol
• 英文别名: 2-isopropyl-1,3-dimethylbenzene；isopropyl-2,6-dimethylbenzene；2-Isopropyl-m-xylol；2,6-Dimethylisopropylbenzene；1,3-dimethyl-2-propan-2-ylbenzene
• CAS: 14411-75-7
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: IVCIQLTVLDOHKA-UHFFFAOYSA-N

物化性质

• 熔点：
  -44.72°C (estimate)
• 沸点：
  199°C
• 密度：
  0.8860

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-2-isopropyl-benzol 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 生成 2-Isopropyl-3-methylbenzalbromid
  参考文献：
  名称：

  Nasipuri,D.; De Dalal,l., Journal of the Chemical Society. Perkin transactions I, 1975, p. 2052 - 2055

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-dimethylisopropenylbenzene 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 1,3-Dimethyl-2-isopropyl-benzol
  参考文献：
  名称：

  Organic photochemistry. 35. Structural effects on the nonradiative decay of alkylbenzenes. The nature of the ".alpha.-substitution effect"

  摘要：

  DOI：

  10.1021/ja00452a025

文献信息

• Efficient cross-coupling of aryl/alkenyl triflates with acyclic secondary alkylboronic acids
  作者：Tengda Si、Bowen Li、Wenrui Xiong、Bin Xu、Wenjun Tang

  DOI：10.1039/c7ob02531a

  日期：——

  Aryl–secondary alkyl cross-coupling with aryl sulfonate esters as coupling partners remains a significant challenge. Efficient cross-coupling between aryl/alkenyl triflates and acyclic secondary alkylboronic acids is realized for the first time to provide a series of sterically congested acyclic secondary alkyl arenes/olefins in good to excellent yields. The employment of sterically bulky P,PO ligand L1/L2 is

  芳基-仲烷基与芳基磺酸酯作为偶联伙伴的交叉偶联仍然是一个巨大的挑战。首次实现了芳基/烯基三氟甲磺酸酯与无环仲烷基硼酸之间的有效交叉偶联，从而以良好或优异的收率提供了一系列空间上拥挤的无环仲烷基芳烃/烯烃。使用空间庞大的P，P O配体L1 / L2对于高收率和选择性至关重要。该方法实现了男性避孕药和PAF拮抗剂棉酚的关键中间体的简明和4步合成。
• Halogen‐Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions
  作者：Nardana Sivendran、Nico Pirkl、Zhiyong Hu、Angelino Doppiu、Lukas J. Gooßen

  DOI：10.1002/anie.202110450

  日期：2021.11.15

  Halide-bridged 1- and 2-methylnaphthyl palladium dimers are presented as convenient, yet highly efficient palladium sources for cross-coupling catalysis. The bench-stable complexes smoothly react with various ligands yielding monoligated palladium precatalysts. These display record-setting activity in various catalytic reactions, clearly beyond that achievable by ligand screening alone.

  卤化物桥接的 1-和 2-甲基萘基钯二聚体被认为是用于交叉偶联催化的方便且高效的钯源。台架稳定的配合物与各种配体顺利反应，产生单配位钯预催化剂。这些在各种催化反应中显示出创纪录的活性，明显超出了仅通过配体筛选所能达到的水平。
• Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
  作者：Carlos Vila、Massimo Giannerini、Valentín Hornillos、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1039/c3sc53047g

  日期：——

  Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C–C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

  钯催化的二级C(sp3)有机金属试剂交叉偶联反应一直是有机合成中的一个长期挑战，主要由于与不期望的异构化或还原产物形成相关的问题。基于我们最近开发的与有机锂试剂的催化C–C键形成反应，本文呈现了一种钯催化的二级烷基锂试剂与芳基和烯基溴化物的交叉偶联反应。该反应在室温下进行，反应时间短，选择性和产率均很高。这一方法也适用于受阻的芳基溴化物，而这在金属催化的交叉偶联反应中是一个主要挑战。
• Efficient Synthesis of Sterically Hindered Arenes Bearing Acyclic Secondary Alkyl Groups by Suzuki-Miyaura Cross-Couplings
  作者：Chengxi Li、Tianyu Chen、Bowen Li、Guolan Xiao、Wenjun Tang

  DOI：10.1002/anie.201411518

  日期：2015.3.16

  Bulky P,PO ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki–Miyaura cross‐couplings between di‐ortho‐substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho‐alkoxy di‐ortho‐substituted

  庞大的P，P = O配体设计用于在位阻芳基卤化物和烷基硼酸之间的交叉偶联过程中抑制异构化和还原副反应。高产率地实现了二邻位取代的芳基溴化物和无环仲烷基硼酸之间的Suzuki-Miyaura交叉偶联。该方法还能够以优异的收率制备带有异丙基的邻烷氧基双邻取代芳烃。合成方法的实用性已在雌酮的后期修饰中以及在向棉酚的新合成途径中的应用中得到了证明。
• Isopropylation of Xylenes Catalyzed by Ultrastable Zeolite Y (USY) and Some Other Solid Acid Catalysts
  作者：Chitta Ranjan Patra、Rajiv Kumar

  DOI：10.1006/jcat.2002.3776

  日期：2002.12

  (1-methylethyl) benzenes, or in other words dimethyl cumenes (DMCs), using isopropanol as alkylating agent. The effect of reaction temperature, space velocity, substrate-to-alkylating-agent molar ratio, and time-on-stream on conversion of xylene isomers and selectivity to dimethyl cumene was studied. Isopropylation of xylenes over USY gives quite high (80 to 95%) DMC selectivity among the dimethyl cumenes, along

  使用异丙醇作为烷基化剂，在超稳定的沸石Y（USY）催化剂上进行所有三种二甲苯异构体的异丙基化，得到相应的二甲基（1-甲基乙基）苯，或换句话说，二甲基枯烯（DMC）。研究了反应温度，空速，底物对烷基化试剂的摩尔比和生产时间对二甲苯异构体转化率和对二甲基枯烯选择性的影响。在USY上对二甲苯的异丙基化可在二甲基枯烯中获得相当高的DMC选择性（80％至95％），相对于限制试剂，即在相对较低的反应温度下，异丙基化试剂，总产品中DMC的产率为70-90％（ 423±10 K）和相当高的二甲苯转化率（理论最大值的85–97％）。固体酸催化剂H-Y，H-β，H-丝光沸石，间二甲苯。